2-Cyclohexene-1-one derivatives

ABSTRACT

A compound of the formula ##SPC1## 
     Wherein 
     R 1  is selected from the group consisting of phenyl and straight or branched chain alkyl; 
     R 2  is selected from the group consisting of straight or branched chain lower alkyl, straight or branched chain lower alkenyl, lower alkynyl, lower alkoxymethyl, lower alkylthiomethyl and benzyl; 
     X is a same or different substituent which is selected from the group consisting of straight or branched chain alkyl, lower alkoxycarbonyl, phenyl, substituted phenyl having at least one substituent selected from the group consisting of halogen, methyl and methoxy, styryl, furyl, thienyl and --(CH 2 )m-- in which m is an integer from 1 to 6; 
     n is 0 or an integer from 1 to 6; 
     Z is a substituent selected from the group consisting of R-A- and T in which R is selected from the group consisting of lower alkyl, phenyl, substituted phenyl having at least one substituent selected from the group consisting of halogen, methyl, methoxy and nitro, benzyl, phenoxymethyl and phenoxymethyl substituted with at least one halogen; 
     A is selected from the group consisting of carbonyl and sulfonyl; 
     T is selected from the group consisting of lower alkyl and benzyl; 
     Is useful as herbicide.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to novel compounds of2-cyclo-hexene-1-one-derivatives, to a process for the preparationthereof and their uses as selective herbicide.

More particularly, this invention is directed to compositions andmethods employing, as an active herbicidal ingredient, at least onecompound of the formula: ##SPC2##

Where

R₁ is selected from the group consisting of phenyl and straight orbranched chain alkyl;

R₂ is selected from the group consisting of straight or branched chainlower alkyl, straight or branched chain lower alkenyl, lower alkynyl,lower alkoxymethyl, lower alkylthiomethyl and benzyl;

X is a same or different substituent which is selected from the groupconsisting of straight or branched chain alkyl, lower alkoxycarbonyl,phenyl, substituted phenyl having at least one substituent selected fromthe group consisting of halogen, methyl and methoxy, styryl, furyl,thienyl and --(CH.sub. 2)m-- in which m is an integer from 1 to 6;

n is 0 or an integer from 1 to 6;

Z is a substituent selected from the group consisting of R--A-- and T inwhich R is selected from the group consisting of lower alkyl, phenyl,substituted phenyl having at least one substituent selected from thegroup consisting of halogen, methyl, methoxy and nitro, benzyl,phenoxymethyl and phenoxymethyl substituted with at least one halogen;

A is selected from the group consisting of carbonyl and sulfonyl;

T is selected from the group consisting of lower alkyl and benzyl.

Preferred for use according to this invention because they are effectiveas herbicides at lower rates of application are compounds of the formula##SPC3##

Where:

R is phenyl or substituted phenyl;

R₁ is ethyl or propyl;

R₂ is ethyl, propyl, allyl or propargyl.

Especially preferred for use because of their herbicidal effectivenessare:

2-(N-allyloxypropionimidoyl)-3-(4-chlorobenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one,

2-(N-allyloxybutyrimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclo-hexene-1-one,

2-(N-allyloxypropionimidoyl)-3-(4-nitrobenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one,2-(N-allyloxypropionimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclohexene-1-one

3-benzoyloxy-5,5-dimethyl-2-N-propargyloxybutyrimidoyl-2-cyclohexene-1-one,

2-(N-allyloxypropionimidoyl)-3-(3-methoxybenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one,

2-(N-allyloxypropionimidoyl)-3-(3-chlorobenzyloxy)-5,5-dimethyl-2-cyclohexene-1-one,

4-(4-methylbenzoyloxy)-5,5-dimethyl-2-(N-propargyloxybutyrimidoyl)-2-cyclohexene-1-one,

The compounds of this invention can be prepared in accordance with thefollowing equation: ##SPC4##

wherein R₁, R₂, R, X, n, A, T and Z are as previously defined and Yrepresents halogen atom.

The starting material (III) can be prepared in accordance with thefollowing equation: ##SPC5##

Almost all of the compounds having above formula (VII) are known andthey can be prepared by methods heretofore described in the literature.

For example, methods for preparing above substitutedcyclohexane-1,3-diones (VII) are illustrated by the following equations:##SPC6##

wherein r₁, r₂, r₃ and r are lower alkyl, r₄ is lower alkyl, phenyl,substituted phenyl, styryl, furyl or thienyl. With respect to the aboveformula (III) it is expected that the said compound has the followingthree structural formulae because of tautomerism: ##SPC7##

In practical method first of all an alkali metal salt of the startingcompound (III) is prepared by treating it with sodium or potassiumhydroxide in an aqueous solution or an organic solvent.

The said alkali metal salt is made to react with the compound of generalformula (IV), (V) or (VI) in an inert solvent after separating it fromthe reaction mixture or as it is.

As an inert solvent, acetone, ether, alcohol, benzene, toluene,chloroform and a ethyl acetate etc. are used.

Ordinarily, temperatures from the range of -20° C to the boiling pointof the solvent, and preferably below room temperature, aresatisfactorily employed for the above reaction and the reactionterminates between about 15 minutes and 5 hours.

After finishing the reaction, the employed solvent, if necessary, isreplaced with the other solvent and then, the reaction mixture is washedwith alkaline solution and water and dried, and further, solvent isdistilled under reduced pressure, thereby the crude product is obtainedas crystal or liquid.

The crude product can be purified by recrystallization or columchromatography. A structural formula of the resulting purified compoundcan be confirmatively identified by means of an elementary analysis, NMRspectrum or IR spectrum etc.

In order that the invention may be better understood, the followingexamples are given:

AN EXPLANATION OF THE DRAWING

FIG. 1 is the infrared spectrum of Compound No. 1.

FIG. 2 is the infrared spectrum of Compound No. 2.

FIG. 3 is the infrared spectrum of Compound No. 5.

FIG. 4 is the infrared spectrum of Compound No. 8.

FIG. 5 is the infrared spectrum of Compound No. 14.

FIG. 6 is the infrared spectrum of Compound No. 16.

FIG. 7 is the infrared spectrum of Compound No. 38.

EXAMPLE 13-Benzoyloxy-2-(N-ethoxypropionimidoyl)-5,5-dimethyl-2-cyclohexene-1-one

2.4 g of2-[1-(N-ethoxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione weredissolved in 20ml of acetone of 2 ml of aqueous solution containing 0.4g of dissolved sodium hydroxide was added in above resulting solution atroom temperature with stirring. After cooling the resulting solution,1.4 g of benzyol chloride was added dropwise to it at a temperaturerange of -5° to 0° C and it was stirring for about 15 minutes. Further,the resulting solution was stirring for about 20 minutes at roomtemperature. After finishing the reaction, said acetone was distilledoff under reduced pressure and the residual material was dissolved in 20ml of chloroform.

The resulting chloroform layer was washed with 10 ml of aqueous solutioncontaining 2% of sodium hydroxide and with 10 ml of water. The saidchloroform layer was dried with magnesium sulfate. The chloroformsolution was filtered and chloroform was distilled off under reducedpressure and thereby,3-benzoyloxy-2-(N-ethoxypropionimidoyl)-5,5-dimethyl-2-cyclohexene-1-onewas obtained as a colorless liquid.

Yield: 3.3 g (96%)

Refractive index: n_(D) ³¹ :1.5269

EXAMPLE 23-(4-chlorobenzoyloxy)-2-(N-ethoxypropionimidoyl)-5,5-dimethyl-2-cyclohexene-1-one

The same reaction procedures as Example 1 were carried out by using 2.4g of 2-[1-(N-ethoxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dioneand 1.75 g of 4-chlorobenzoylchloride, and chloroform was distilled offunder reduced pressure and thereby the desired product as a whitecrystal was obtained after recrystallization the residual material fromn-hexane.

Yield: 3.5 g (93%)

Melting point: 60° - 62° C

EXAMPLE 3

The following compounds (C) can be synthesized by the method of Example1 substituting the appropriate substituted cyclohexane 1,3-dione (A) for2-[1-(N-ethoxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione andthe appropriate acyl halide or sulfonyl halogenide (B) for benzoylchloride.

Compound No. 2

A. 2[1-(N-allyloxyamino)hexylidene]-5,5-dimethylcyclohexane-1,3-dione,2.9 g

B. methanesufonylchloride, 1.5 g

C.2-(N-allyloxyhexaneimidoyl)-5,5-dimethyl-3-methonesulfonyloxy2-(cyclohexene-1-one,colorless liquid

Yield: 3.2 g (87%)

Refractive index: n_(D) ³¹ :1.4960

Compound No. 18

A. 2-[1-(N-allyloxyamino)benzylidene]-5,5-dimethylcyclohexane-1,3-dione, 3.0 g

B. benzoyl chloride, 1.4 g

C.2-(N-allyloxybenzimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclohexene-1-one,light yellow liquid

Yield: 3.3 g (93%)

Refractive index: n_(D) ¹⁹.5 :1.5770

Compound No. 29

A. 2-[1-(N-ethoxyamino)propylidene] -5,5-dimethylcyclohexane-1,3-dione,2.4 g

B. 4-methyl-benzoylchloride, 1.5 g

C.2-(N-ethoxypropionimidoyl)-3-(4-methylbenzoyloxy)-5,5-dimethyl-3-cylohexene-1-one,yellow liquid

Yield: 3.2 g (90%)

Refractive index: n_(D) ³¹ :1.5139

Compound No. 31

A. 2-[1-(N-ethoxyamino)hexylidene]-5,5-dimethylcyclohexane-1,3-dione,2.8 g

B. tosylchloride, 1.9 g

C.2-(N-ethoxyhexaneimidoyl)-3-tosyloxy-5,5-dimethyl-2-cyclohexene-1-one,colorless liquid

Yield: 4.2 g (92%)

Refractive index: n_(D) ³¹ :1.5215

Compound No. 33

A. 2-[1-(N-allyloxyamino)butylidene]-5,5-dimethylcyclohexane-1,3-dione,2.65 g

B. 3-methoxybenzoylchloride, 1.7 g

C.2-(N-allyloxybutyrimidoyl)-3-(2-methoxybenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one,yellow liquid

Yield: 3.8 g (95%)

Refractive index: n_(D) ³¹ :1.5363

Compound No. 38

A. 2-[1-(N-allyloxyamino)propylidene]-cyclohexane-1,3-dione, 2.2 g

B. benzoylchloride, 1.4 g

C. 2-(N-allyloxypropionimidoyl)-3-benzoyloxy-3-cyclohexene-1-one,colorless liquid

Yield: 3.1 g (95%)

Refractive index: n_(D) ²⁶ :1.5479

Compound No. 39

A. 2-[1-(N-allyloxyamino)propylidene]-5-methylcyclohexane-1,3-dione, 2.4g

B. benzoylchloride, 1.4 g

C.2-(N-allyloxypropionimidoyl)-3-benzoyloxy-5-methyl-2-cyclohexene-1-one,orange liquid

Yield: 3.3 g (97%)

Refractive index: n_(D) ²⁰ :1.5362

Compound No. 43

A. 2-[1-(N-ethoxyamino)propylidene]-5-hexylcyclohexane-1,3-dione, 2.95 g

B. benzenesulfonyl chloride, 1.7 g

C.2-(N-ethoxypropionimidoyl)-3-phenylsulfonyloxy-5-hexyl-2-cyclohexene-1-one,light yellow liquid

Yield: 4.1 g (94%)

Refractive index: n_(D) ¹⁸ :1.5221

Compound No. 44

A. 2-[1-(N-allyloxyamino)propylidene]-5-phenylcyclohexane-1,3-dione, 3.0g

B. benzoylchloride, 1.4 g

C.2-(N-allyloxypropionimidoyl)-3-benzoyloxy-5-phenyl-2-cyclohexene-1-one,light yellow liquid

Yield: 3.7 g (92%)

Refractive index: n_(D) ¹⁹.5 :1.5775

EXAMPLE 4

The following compounds (C) can be synthesized by the method of Example2 substituting the appropriate substituted cyclohexane-1,3-dione (A) for2-[1-(N-ethoxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione andthe appropriate acyl halide or sulfonyl halogenide (B) for benzoylchloride.

Compound No. 36

A. 2-[1-(N-allyloxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione,2.5 g

B. 4-nitrobenzoyl chloride, 1.85 g

C.2-(N-allyloxypropionimidoyl)-5,5-dimethyl-3-(4-nitrobenzoyloxy)-2-cyclohexene-1-one,white crystal

Yield: 3.8 g (95%)

Melting point: 78° - 80° C

Compound No. 12

A.2-[1-(N-benzyloxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione,3.0 g

B. benzoyl chloride, 1.4 g

C.2-(N-benzyloxypropionimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclohexene-1-one,white crystal

Yield: 3.8 g (95%)

Melting point: 54° - 55° C

EXAMPLE 52-(N-allyloxybutyrimidoyl)-5,5-dimethyl-3-propionyloxy-2-cyclohexene-1-one

5.4 g of2-[1-(N-allyloxyamino)butylidene]-5,5-dimethylcyclohexane-1,3-dione weredissolved in 40 ml of acetone and 4 ml of aqueous solution containing0.8 g of dissolved sodium hydroxide were added in above resultingsolution at room temperature with stirring. Dried sodium metal salt of2-[1-(N-allyloxyamino) butylidene]-5,5-dimethylcyclohexane-1,3-dione wasobtained by distillating acetone under reduced pressure. 40 ml of driedacetone were added to said sodium salt and 1.8 g of propionyl chloridewas added dropwise to the resulting solution at a temperature range of-5° to 0° C after cooling it. After stirring the resulting solution forabout 30 minutes, acetone was distilled under reduced pressure and theresidual material was dissolved in 40 ml of ether. Then, the resultingether layer was dried with magnesium solfate after washing it with 20 mlof aqueous solution containing 2% of sodium hydroxide and 20 ml ofwater. The said ether solution was filtered and2-(N-allyloxybutyrimidoyl)-5,5-dimethyl-3-propionyloxy-2-cyclohexene-1-onewas obtained as a colorless liquid by distillating ether under reducedpressure.

Yield: 5.2 g (80%)

Refractive index: n_(D) ³¹ :1.4762

EXAMPLE 63-Benzoyloxy-2-(N-ethoxybutyrimidoyl)-5,5-dimethyl-6-methoxycarbonyl-2-cyclohexene-1-one

To a solution of5,5-dimethyl-2-(N-ethoxyaminobutylidene)-4-methoxycarbonylcyclohexane-1,3-dione(3.1g) in 30 ml of acetone, 1 ml of aqueous solution containing 0.4 g ofdissolved sodium hydroxide was added at room temperature and thenbenzoyl chloride (1.4g) was added. After stirring for 5 hours, thereaction mixture was poured into ice-water and extracted withchloroform. The extract was washed with one normal sodium hydroxide anddried over magnesium sulfate. The solvent was removed in vacuo and thedesired product as an oily substance was obtained.

Yield: 2.8 g

Refractive index: n_(D) ²⁴.5 :1.5165

EXAMPLE 7

The following compound (C) can be synthesized by the method of Example 6substituting the appropriate substituted cyclohexane-1,3-dione (A) for5,5-dimethyl-2-(N-allyloxyaminobutylidene)-4-methoxycarbonylcyclohexane-1,3-dioneand the appropriate acyl halide or sulfonyl halogenide (B) for benzoylchloride.

Compound No. 105

A.2-(1-allyloxyaminopropylidene)-4-ethoxycarbonyl-4-ethylcyclohexane-1,3-dione,1.6 g

B. benzoyl chloride, 0.7 g

C.2-(N-allyloxypropionimidoyl)-3-benzyloxy-6-ethoxycarbonyl-6-ethyl-2-cyclohexene-1-one

Yield: 1.3 g

Refractive index: n_(D) ²⁴ 1.5225

Compound No. 84

A.2-(1-allyloxyaminopropylidene)-5,5-dimethyl-4-ethoxycarbonyl-cyclohexane-1,3-dione,3.2 g

B. 4-chlorobenzoyl chloride, 1.7 g

C.2-(N-allyloxypropionimidoyl)-3-(4-chlorobenzoyloxy)-6-ethoxycarbonyl-5,5-dimethyl-2-cyclohexene-1-one,

Yield: 2.3 g

Refractive index: n_(D) ²² 1.5348

Compound No. 117

A. 2-(1-allyloxyaminopropylidene)-5-styryl-cyclohexane-1,3-dione, 3.3 g

B. benzoyl chloride, 1.4 g

C.2-(N-allyloxypropionimidoyl)-3-benzoyloxy-5-styryl-2-cyclohexene-1-one

Yield: 1.5 g

Refractive index: n_(D) ²⁵ 1.5857

Compound No. 118

A. 2-(1-ethoxyaminopropylidene)-5-(2-furyl)cyclohexane-1,3-dione, 1.4 g

B. benzoyl chloride, 0.7 g

C.3-benzoyloxy-2-(N-ethoxypropionimidoyl)-5-(2-furyl)-2-cyclohexene-1-one,

Yield: 1.6 g

Refractive index: n_(D) ¹⁹ 1.5546

Compound No. 107

A.5-(4-chlorophenyl)-2-(1-ethoxyaminopropylidene)-cyclohexane-1,3-dione, 1g

B. benzoyl chloride, 0.42 g

C.3-benzoyloxy-5-(4-chlorophenyl)-2-(N-ethoxypropionimidoyl)-2-cyclohexene-1-one

Yield: 1.2 g

Refractive index: n_(D) ²⁴.5 1.5720

Compound No. 120

A. 2-(1-allyloxyaminopropylidene)-5,5-dimethylcyclohexane-1,3-dione, 2.5g

B. phenylacetyl chloride, 1.5 g

C.2-(N-allyloxypropionimidoyl)-5,5-dimethyl-3-phenylacetoxy-2-cyclohexene-1-one

Yield: 1.8 g

Refractive index: n_(D) ²² 1.5249

Compound No. 122

A. 2-(1-ethoxyaminopropylidene)-4-isobutylcyclohexane-1,3-dione, 1.3 g

B. phenylacetyl chloride, 0.8 g

C.2-(N-ethoxypropionimidoyl)-6-isobutyl-3-phenylacetoxy-2-cyclohexene-1-one

Yield: 0.4 g

Refractive index: n_(D) ²⁴ 1.5172

Compound No. 125

A.5,5-dimethyl-2-(1-methylthiomethoxyaminopropylidene)-cyclohexane-1,3-dione,1.4 g

B. benzoyl chloride, 0.7 g

C.3-benzoyloxy-5,5-dimethyl-2-(N-methylthiomethoxypropionimidoyl)-2-cyclohexene-1-one

Yield: 1.2 g

Refractive index: n_(D) ²⁵ 1.5415

Compound No. 127

A.5-isopropyl-2-(1-methylthiomethyloxyaminopropylidene)-cyclohexane-1,3-dione,1.4 g

B. benzoyl chloride, 0.7 g

C.3-benzoyloxy-5-isopropyl-2-(N-methylthiomethyloxypropionimidoyl)-2-cyclohexene-1-one

Yield: 1.7 g

Refractive index: n_(D) ²³ 1.5495

Compound 130

A.2-(1-butoxymethyloxyaminopropylidene)-5,5-dimethylcyclohexane-1,3-dione,2 g

B. methylsulfonyl chloride, 0.7 g

C.2-(N-butoxymethyloxypropionimidoyl)-5,5-dimethyl-3-methylsulfonyloxy-2-cyclohexene-1-one

Yield: 1.1 g

Refractive index: n_(D) ²³ 1.4885

EXAMPLE 85-(2,4-Dichlorophenyl)-2-(N-ethoxypropionimidoyl)-3-methylsulfonyloxy-2-cyclohexene-1-one

To a solution of5-(2,4-dichlorophenyl)-2-(1-ethopyaminopropylidene)-cyclohexane-1,3-dione(1.4 g) in acetone (30 ml), sodium hydroxide (0.2 g) in water (2 ml) wasadded at room temperature and then methanesulfonyl chloride (0.5 g) wasadded. After stirring for 1 hr, the reaction mixture was poured intoice-water and extracted with chloroform. The extract was washed with onenormal sodium hydroxide and dried over magnesium sulfate. The solventwas removed in vacuo and an oily substance (0.5 g) was obtained. Thedesired product having a melting point of 73° to 75° C was obtained ascolorless prisms by recrystallizing said oily substance from n-hexane.

EXAMPLE 9

The following compound (C) can be synthesized by the method of Example 8substituting the appropriate substituted cyclohexane-1,3-dione (A) for5-(2,4-dichlorophenyl)-2-(1-ethoxyaminopropylidene)cyclohexane-1,3-dione and the appropriate acyl halide or sulfonylhalogenide (B) for methanesulfonyl chloride.

Compound No. 135

A. 2-(1-allyloxyaminopropylidene)-5,5-dimethylcyclohexane-1,3-dione, 2.5g

B. benzoyl chloride, 2.1 g

C.2-(N-allyloxypropionimidoyl)-3-(2,4-dichlorobenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one,colorless crystal

Melting point: 74° - 75° C

Compound No. 136

A. 5,5-dimethyl-2-(1-propargyloxyaminobutylidene)cyclohexane-1,3-dione,2.5 g

B. 3,6-dichloro-2-methoxybenzoylchloride, 2.2 g

C.3-(3,6-dichloro-2-methoxybenzoyloxy)-5,5-dimethyl-2-(N-propargyloxybutyrimidoyl)-2-cyclohexene-1-one,colorless crystal,

Melting point: 87° - 88° C

EXAMPLE 103-Acetoxy-6-ethoxycarbonyl-2-(N-ethoxypropionimidoyl)-2-cyclohexene-1-one

Sodium salt of2-(1-ethoxyaminopropylidene)-4-ethoxycarbonyl-5,5-dimethylcyclohexane-1,3-dione(3.1 g) was suspended in 50 ml of acetone and acetylchloride (0.8 g) wasadded to it at room temperature. After stirring for 3 hours, thereaction mixture was poured into ice-water and extracted withchloroform. The extract was washed with one normal sodium hydroxide anddried over magnesium sulfate. The solvent was removed is vacuo and thedesired product was obtained as an oily substance.

Yield: 1.2 g

Refractive index: n_(D) ¹⁸ 1.4848

EXAMPLE 112-(N-allyloxybutyrimidoyl)-5,5-dimethyl-3-methoxy-2-cyclohexene-1-one

Silver salt of2-(1-allyloxyaminobutylidene)-5,5-dimethylcyclohexane-1,3-dione (25 g)was suspended in 100 ml of ether and methyl iodide (34 g) was added. Themixture was refluxed for 6 hours with stirring. After filtering silveriodide, the solvent was removed in vacuo and then poured into water. Theoil thus separated was extracted with chloroform and washed with onenormal sodium hydroxide and dried over magnesium sulfate. The solventwas removed in vacuo and the desired product was obtained as an oilysubstance.

Yield: 11.5 g

Refractive index: n_(D) ²⁶ 1.3532

EXAMPLE 122-(N-allyloxypropionimidoyl)-3-benzyloxy-5,5-dimethyl-2-cyclohexene-1-one

To a solution of2-(1-allyloxyaminopropylidene)-5,5-dimethylcyclohexane-1,3-dione (2.5 g)in acetone (30 ml), sodium hydroxide (0.4 g) in water (2 ml) was addedat room temperature and then benzyl bromide (2.0 g) was added. Afterstirring for 10 hours at 60° C the reaction mixture was poured intoice-water and extracted with chloroform. The extract was washed with onenormal sodium hydroxide and dried over magnesium sulfate. The solventwas removed in vacuo and an oily substance which solidified on standingat 0° C was obtained. Recrystallization from the mixture of methanol andwater gave the desired product as crystal.

Melting point: 60.5° - 61.5° C

EXAMPLE 137-(N-allyloxypropionimidoyl)-6-benzoyloxy-1,2,3,4,5,8,4a,8a-octahydronaphthalene-8-one

To a solution of 2-(1-allyloxyaminopropylidene)decaline-1,3-dione (2 g)in acetone (30 ml), sodium hydroxide (0.2 g) in water (1 ml) was addedat room temperature and then benzoylchloride (0.7 g) was added. Afterstirring for 5 hours, the reaction mixture was poured into ice-water andextracted with chloroform. The extract was washed with one normal sodiumhydroxide and dried over magnesium sulfate. The solvent was removed invacuo and an oily substance (1.8 g) was obtained.

Refractive index: n_(D) ²⁰.5 1.5499 (Another nomenclature of CompoundNo. 133)

EXAMPLE 144-(N-allyloxypropionimidoyl)-3-benzoyloxy-5-oxo-3-cyclohexenespirocyclohexane

To a solution of4-(1-allyloxyaminopropylidene)spirobicyclohexane-3,5-dione (1.5 g) inacetone (30 ml), sodium hydroxide (0.2 g) in water (1 ml) was added atroom temperature and then benzoylochloride (0.7 g) was added. Afterstirring for 5 hr, the reaction mixture was poured into ice-water andextracted with chloroform. The extract was washed with one normal sodiumhydroxide and dried over magnesium sulfate. The solvent was removed invacuo and oily substance (0.8 g) was obtained.

Refractive index: n_(D) ²³ 1.5475 (Another nomenclature of Compound No.134)

In addition to the above mentioned compounds described in the precedingexample, some typical compounds of the present invention are listed inTable 1.

                  Table 1                                                         ______________________________________                                        Com-                                                                          pound                             Physicalt                                   No.             Chemical Name     constant                                    ______________________________________                                               2-(N-ethoxybutyrimidoyl)-                                              1      3-methylsulfonyloxy-5,5-                                                                             n.sub.D.sup.31 1.4896                                  dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-allyloxyhexanimidoyl)-                                            2      3-methylsulfonyloxy-5,5-                                                                             n.sub.D.sup.31 1.4960                                  dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-allyloxybutyrimidoyl)-                                            3      3-propionyloxy-5,5-dimethyl-                                                                         n.sub.D.sup.31 1.4762                                  2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            4      3-ethylsulfonyloxy-5,5-                                                                              n.sub.D.sup.29.5 1.4874                                dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-allyloxyacetimidoyl)-                                             5      3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.31 1.5289                                  2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            6      3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.31 1.5269                                  2-cyclohexene-1-one                                                           2-(N-propoxypropionimidoyl)-                                           7      3-benzoyloxy-5,5-dimethyl-2-                                                                         n.sub.D.sup.24.5 1.5350                                cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          8      3-benzoyloxy-5,5-dimethyl-2-                                                                         n.sub.D.sup.29 1.5338                                  cyclohexene-1-one                                                             2-(N-propargyloxypropion-                                              9      imidoyl)-3-benzoyloxy-5,5-                                                                           n.sub.D.sup.18.5 1.5401                                dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-butoxypropionimidoyl)-                                            10     3-benzoyloxy-5,5-dimethyl-2-                                                                         n.sub.D.sup.18.5 1.5249                                cyclohexene-1-one                                                             2-(N-isobutoxypropionimidoyl)-                                         11     3-benzoyloxy-5,5-dimethyl-2-                                                                         d.p.: 64                                               cyclohexene-1-one      to 64° C                                        2-(N-benzyloxypropionimidoyl)-                                         12     3-benzoyloxy-5,5-dimethyl-2-                                                                         m.p.: 54                                               cyclohexene-1-one      to 55° C                                        2-(N-methoxybutyrimidoyl)-3-                                           13     benzoyloxy-5,5-dimethyl-2-                                                                           n.sub.D.sup.23 1.5291                                  cyclohexene-1-one                                                             2-(N-ethoxybutyrimidoyl)-                                              14     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.31 1.5090                                  2-cyclohexene-1-one                                                           2-(N-allyloxybutyrimidoyl)-                                            15     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.31 1.5274                                  2-cyclohexene-1-one                                                           2-(N-propargyloxybutyr-                                                16     imidoyl)-3-benzoyloxy-5,5-                                                                           n.sub.D.sup.31 1.5370                                  dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-ethoxyisobutyrimidoyl)-                                           17     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.23 1.5228                                  2-cyclohexene-1-one                                                           2-(N-allyloxybenzimidoyl)-                                             18     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.19.5 1.5770                                2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            19     3-phenylsulfonylloxy-5,5-                                                                            n.sub.D.sup.31 1.5259                                  dimethyl-2-cyclohexene-1-                                                     one                                                                           2-(N-allyloxyacetimidoyl)-                                             20     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.31 1.5371                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxypropionimidoyl)-                                            21     3-(4-chlorobenzoyloxy)-5,5-                                                                          m.p.: 60                                               dimethyl-2-cyclohexene-1-one                                                                         to 62° C                                        2-(N-allyloxypropionimidoyl)-                                          22     3-(4-chlorobenzoyloxy)-5,5-                                                                          m.p.: 53                                               dimethyl-2-cyclohexene-1-one                                                                         to 54° C                                        2-(N-ethoxybutyrimidoyl)-3-                                            23     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.31 1.5295                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-isopropoxybutyrimidoyl)-                                          24     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.31 1.5252                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxyhexanimidoyl)-3-                                            25     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.31 1.5205                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          26     3-(4-chlorophenylsulfonyloxy)-                                                                       n.sub.D.sup.31 1.5366                                  5,5-dimethyl-2-cyclohexene-1-                                                 one                                                                           2-(N-methoxybutyrimidoyl)-                                             27     3-(4-chlorophenylsulfonyloxy)-                                                                       n.sub.D.sup.23 1.5362                                  5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-ethoxyhexanimidoyl)-                                              28     3-(4-chlorophenylsulfonyloxy)-                                                                       n.sub.D.sup.31 1.5248                                  5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            29     3-(4-methylbenzoyloxy)-5,5-                                                                          n.sub.D.sup.31 1.5139                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxybutyrimidoyl)-                                              30     3-(4-methylbenzoyloxy)-5,5-                                                                          n.sub.D.sup.31 1.5212                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxyhexanimidoyl)-                                              31     3-tosyloxy-5,5-dimethyl-2-                                                                           n.sub.D.sup.31 1.5215                                  cyclohexene-1-one                                                             2-(N-isopropoxybutyrimidoyl)-                                          32     3-tosyloxy-5,5-dimethyl-2-                                                                           n.sub.D.sup.31 1.5192                                  cyclohexene-1-one                                                             2-(N-allyloxybutyrimidoyl)-                                            33     3-(2-methoxybenzoyloxy)-5,5-                                                                         n.sub.D.sup.31 1.5363                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxyhexanimidoyl)-                                            34     3-(2-methoxybenzoyloxy)-5,5-                                                                         n.sub.D.sup.30 1.5264                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          35     3-(3-methoxybenzoyloxy)-5,5-                                                                         n.sub.D.sup.31 1.5294                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          36     3-(4-nitrobenzoyloxy)-5,5-                                                                           m.p.: 78                                               dimethyl-2-cyclohexene-1-one                                                                         to 80° C                                        2-(N-propoxypropionimidoyl)-                                           37     3-(4-nitrophenylsulfonyloxy)-                                                                        n.sub.D.sup.24.5 1.5375                                5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-allyloxypropionimidoyl)-                                          38     3-benzoyloxy-2-cyclohexene-1-                                                                        n.sub.D.sup.26 1.5479                                  one                                                                           2-(N-allyloxypropionimidoyl)-                                          39     3-benzoyloxy-5-methyl-2-                                                                             n.sub.D.sup.20 1.5362                                  cyclohexene-1-one                                                             2-(N-ethoxyacetimidoyl)-3-                                             40     benzoyloxy-5-methyl-2- n.sub.D.sup.18.5 1.5389                                cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          41     3-methylsulfonyloxy-5-hexyl-                                                                         n.sub.D.sup.18 1.4987                                  2-cyclohexene-1-one                                                           2-(N-ethoxybutyrimidoyl)-3-                                            42     benzoyloxy-5-hexyl-2-  n.sub.D.sup.18.5 1.5209                                cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-                                            43     3-phenylsulfonyloxy-5-hexyl-                                                                         n.sub.D.sup.18 1.5221                                  2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          44     3-benzoyloxy-5-phenyl-2-                                                                             n.sub.D.sup.19.5 1.5775                                cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          45     3-(4-methylbenzoyloxy)-5,5-                                                                          m.p.: 46                                               dimethyl-2-cyclohexene-1-one                                                                         to 47° C                                        2-(N-allyloxypropionimidoyl)-                                          46     3-(3-methoxybenzoyloxy)-5,5-                                                                         m.p.: 46                                               dimethyl-2-cyclohexene-1-one                                                                         to 47° C                                        2-(N-allyloxypropionimidoyl)-                                          47     3-(2-methoxybenzoyloxy)-5,5-                                                                         n.sub.D.sup.22 1.5371                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          48     3-(3-nitrobenzoyloxy)-5,5-                                                                           m.p.: 76                                               dimethyl-2-cyclohexene-1-one                                                                         to 78° C                                        2-(N-allyloxypropionimidoyl)-                                          49     3-(2-methylbenzoyloxy)-5,5-                                                                          m.p.: 37                                               dimethyl-2-cyclohexene-1-one                                                                         to 38° C                                        2-(N-allyloxypropionimidoyl)-                                          50     3-phenylsulfonyloxy-5,5-                                                                             n.sub.D.sup.22 1.5327                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          51     3-(4-phenylsulfonyloxy-5,5-                                                                          n.sub.D.sup.22 1.5310                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          52     3-(3-chlorobenzoyloxy)-5,5-                                                                          m.p.: 39                                               dimethyl-2-cyclohexene-1-one                                                                         to 40° C                                        2-(N-propargyloxybutyrimidoyl)-                                        53     3-(4-chlorobenzoyloxy)-5,5-                                                                          m.p.: 87                                               dimethyl-2-cyclohexene-1-one                                                                         to 88° C                                        2-(N-propargyloxybutyrimidoyl)-                                        54     3-ethylsulfonyloxy-5,5-                                                                              n.sub.D.sup.19 1.5046                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-propargyloxybutyrimidoyl)-                                        55     3-methylsulfonyloxy-5,5-                                                                             n.sub.D.sup.19 1.5101                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-propargyloxybutyrimidoyl)-                                        56     3-(4-nitrobenzoyloxy)-5,5-                                                                           m.p.: 88                                               dimethyl-2-cyclohexene-1-one                                                                         to 89° C                                        2-(N-allyloxypropionimidoyl)-                                          57     3-benzoyloxy-5-isopropyl-2-                                                                          n.sub.D.sup.19 1.5300                                  cyclohexene-1-one                                                             2-(N-propargyloxybutyrimidoyl)-                                        58     3-(3-nitrobenzoyloxy)-5,5-                                                                           n.sub.D.sup.19 1.5468                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-propargyloxybutyrimidoyl)-                                        59     3-(4-methylbenzoyloxy)-5,5-                                                                          m.p.: 67                                               dimethyl-2-cyclohexene-1-one                                                                         to 69° C                                        2-(N-allyloxypropionimidoyl)-                                          60     3-ethylsulfonyloxy-5,5-dimethyl-                                                                     n.sub.D.sup.19 1.5016                                  2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          61     3-methylsulfonyloxy-5,5-                                                                             n.sub.D.sup.19 1.5020                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          62     3-benzoyloxy-5,5,6-trimethyl-                                                                        n.sub.D.sup.23 1.5341                                  2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            63     3-(2-nitro-benzoyloxy)-6-                                                                            n.sub.D.sup.24 1.5345                                  isobutyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-                                          64     3-benzoyloxy-6-propyl-2-                                                                             n.sub.D.sup.19 1.5328                                  cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-3-                                          65     phenylsulfonyloxy-6,6-dimethyl-                                                                      n.sub.D.sup.19 1.5292                                  2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            66     3-(4-chlorobenzoyloxy)-6,6-                                                                          n.sub.D.sup.20 1.5372                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxypropionimidoyl)-                                            67     3-methylsulfonyloxy-6,6-                                                                             n.sub.D.sup.20 1.4960                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxypropionimidoyl)-3-                                        68     propionyloxy-6,6-dimethyl-2-                                                                         n.sub.D.sup.20 1.4918                                  cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          69     3-benzoyloxy-6,6-dimethyl-2-                                                                         n.sub.D.sup.20 1.5357                                  cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          70     3-(4-methylbenzoyloxy)-6-                                                                            n.sub.D.sup.24 1.5298                                  butyl-2-cyclohexene-1-one                                                     2-(N-methallyloxypropionimidoyl)-                                      71     3-methylsulfonyloxy-5,5-dimethyl-                                                                    n.sub.D.sup.23 1.5031                                  2-cyclohexene-1-one                                                           2-(N-methallyloxypropionimidoyl)-                                      72     3-benzoyloxy-5,5-dimethyl-2-                                                                         n.sub.D.sup.23 1.5293                                  cyclohexene                                                                   2-(N-ethoxybutyrimidoyl)-3-                                            73     benzoyloxy-5-methyl-5-phenyl-                                                                        n.sub.D.sup.27.5 1.5598                                2-cyclohexene-1-one                                                           2-(N-ethoxybutyrimidoyl)-3-                                            74     methylsulfonyloxy-5-methyl-                                                                          n.sub.D.sup.27.5 1.5355                                5-phenyl-2-cyclohexene-1-one                                                  2-(N-ethoxypropionimidoyl)-                                            75     3-benzoyloxy-5-propyl-2-                                                                             n.sub.D.sup.27.5 1.5218                                cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          76     3-(2-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.29 1.5338                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-allyloxybutyrimidoyl)-                                            77     3-(2-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.31 1.5269                                  dimethyl-2-cyclohexene-1-one                                                  2-(N-ethoxybutyrimidoyl)-3-                                            78     methylsulfonyloxy-5-methyl-                                                                          n.sub.D.sup.27.5 1.5355                                5-phenyl-2-cyclohexene-1-one                                                  2-(N-ethoxybutyrimidoyl)-3-                                            79     benzoyloxy-5-methyl-5- n.sub.D.sup.27.5 1.5598                                phenyl-2-cyclohexene-1-one                                                    2-(N-ethoxypropionimidoyl)-                                            80     3-acetoxy-5,5-dimethyl-6-                                                                            n.sub.D.sup.18 1.4848                                  ethoxycarbonyl-2-cyclohexene-                                                 1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            81     3-benzoyloxy-5,5-dimethyl-6-                                                                         n.sub.D.sup.18 1.5246                                  ethoxycarbonyl-2-cyclohexene-                                                 1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            82     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.18 1.5282                                  dimethyl-6-ethoxycarbonyl-                                                    2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          83     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.22 1.5282                                  6-ethoxycarbonyl-2-cyclohexene-                                               1-one                                                                         2-(N-allyloxypropionimidoyl)-                                          84     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.22 1.5348                                  dimethyl-6-ethoxycarbonyl-2-                                                  cyclohexene-1-one                                                             2-(N-allyloxybutyrimidoyl)-                                            85     3-benzoyloxy-5,5-dimethyl-                                                                           n.sub.D.sup.21 1.5252                                  6-ethoxycarbonyl-2-cyclohexene-                                               1-one                                                                         2-(N-allyloxybutyrimidoyl)-                                            86     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.21 1.5302                                  dimethyl-6-ethoxycarbonyl-2-                                                  cyclohexene-1-one                                                             2-(N-allyloxyacetionimidoyl)-                                          87     3-benzoyloxy-5,5-dimethyl-6-                                                                         n.sub.D.sup.21.5 1.5237                                ethoxycarbonyl-2-cyclohexene-                                                 1-one                                                                         2-(N-allyloxyacetimidoyl)-3-                                           88     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.21.5 1.5309                                dimethyl-6-ethoxycarbonyl-2-                                                  cyclohexene-1-one                                                             2-(N-ethoxyacetimidoyl)-3-                                             89     benzoyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.22.5 1.5238                                ethoxycarbonyl-2-cyclohexene-                                                 1-one                                                                         2-(N-ethoxyacetimidoyl)-3-                                             90     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.22 1.5290                                  dimethyl-6-ethoxycarbonyl-2-                                                  cyclohexene-1-one                                                             2-(N-ethoxybutyrimidoyl)-3-                                            91     benzoyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.23.5 1.5742                                ethoxycarbonyl-2-cyclohexene                                                  1-one                                                                         2-(N-ethoxybutyrimidoyl)-3-                                            92     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.23.5 1.5265                                dimethyl-6-ethoxycarbonyl-2-                                                  cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-3-                                          93     benzoyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.24 1.5273                                  methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            94     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.23.5 1.5383                                dimethyl-6-methoxycarbonyl-                                                   2-cyclohexene-1-one                                                           2-(N-allyloxybutyrimidoyl)-                                            95     3-benzoyloxy-5,5-dimethyl-6-                                                                         n.sub.D.sup.24.5 1.5195                                methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-allyloxybutyrimidoyl)-                                            96     3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.24.5 1.5303                                dimethyl-6-methoxycarbonyl-2-                                                 cyclohexene-1-one                                                             2-(N-ethoxybutyrimidoyl)-3-                                            97     benozyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.24.5 1.5165                                methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-ethoxybutyrimidoyl)-3-                                            98     (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.24.5 1.5225                                dimethyl-6-methoxycarbonyl-                                                   2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          99     3-benzoyloxy-5,5-dimethyl-6-                                                                         n.sub.D.sup.25 1.5205                                  methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-allyloxypropionimidoyl)-                                          100    3-(4-chlorobenzoyloxy)-5,5-                                                                          n.sub.D.sup.26 1.5248                                  dimethyl-6-methoxycarbonyl-2-                                                 cyclohexene-1-one                                                             2-(N-ethoxyacetimidoyl)-3-                                             101    benzoyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.26 1.5211                                  methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-ethoxyacetimidoyl)-3-(4-                                          102    chlorobenzoyloxy)-5,5-dimethyl-                                                                      n.sub.D.sup.25.5 1.5325                                6-methoxycarbonyl-2-cyclohexene-                                              1-one                                                                         2-(N-allyloxyacetimidoyl)-3-                                           103    benzoyloxy-5,5-dimethyl-6-                                                                           n.sub.D.sup.25 1.5289                                  methoxycarbonyl-2-cyclohexene-                                                1-one                                                                         2-(N-allyloxyacetimidoyl)-3-                                           104    (4-chlorobenzoyloxy)-5,5-                                                                            n.sub.D.sup.26 1.5298                                  dimethyl-6-methoxycarbonyl-                                                   2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          105    3-benzoyloxy-6-ethoxycarbonyl-                                                                       n.sub.D.sup.24 1.5225                                  6-ethyl-2-cyclohexene-1-one                                                   2-(N-ethoxyacetoimidoyl)-3-                                            106    benzoyloxy-6-ethoxycarbonyl-                                                                         n.sub.D.sup.22 1.5108                                  6-ethyl-2-cyclohexene-1-one                                                   2-(N-ethoxypropionimidoyl)-                                            107    3-benozyloxy-5-(4-chlorophenyl)-                                                                     n.sub.D.sup.24.5 1.5720                                2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-3-                                          108    methylsulfonyloxy-5-(4-                                                                              m.p. 106-                                              chlorophenyl)-2-cyclohexene-                                                                         107° C                                          1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            109    3-benozyloxy-5-(4-methoxyphenyl)-                                                                    n.sub.D.sup.24.5 1.5633                                2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            110    3-methylsulfonyloxy-5-(4-                                                                            m.p. 91-                                               methoxyphenyl)-2-cyclohexene-                                                                        92° C                                           1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            111    3-benzoyloxy-5-(4-tolyl)-2-                                                                          n.sub.D.sup.25.5 1.5632                                cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-                                            112    3-methylsulfonyl-5-(4-tolyl)-                                                                        m.p. 114-                                              2-cyclohexene-1-one    115° C                                          2-(N-ethoxypropionimidoyl)-                                            113    3-benzoyloxy-5-(3-chlorophenyl)-                                                                     n.sub.D.sup.25.5 1.5714                                2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-3-                                          114    methylsulfonyl-5-(3-chlorophenyl)-                                                                   m.p. 88-                                               2-cyclohexene-1-one    89° C                                           2-(N-ethoxypropionimidoyl)-                                            115    3-methylsulfonyl-5-(2,4-                                                                             m.p. 73-                                               dichlorophenyl)-2-cyclohexene-                                                                       75° C                                           1-one                                                                         2-(N-ethoxypropionimidoyl)-                                            116    3-benzoyloxy-5-(2,4-   n.sub.D.sup.27.5 1.5693                                dichlorophenyl)-2-cyclohexene-                                                1-one                                                                         2-(N-allyloxypropionimidoyl)-                                          117    3-benzoyloxy-5-styryl-2-                                                                             n.sub.D.sup.25 1.5857                                  cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-                                            118    3-benzoyloxy-5-(2-furyl)-2-                                                                          n.sub.D.sup.19 1.5546                                  cyclohexene-1-one                                                             2-(N-ethoxypropionimidoyl)-                                            119    3-benzoyloxy-5-(2-thienyl)-                                                                          n.sub.D.sup.23.5 1.5729                                2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          120    3-phenylacetoxy-5,5-dimethyl-                                                                        n.sub.D.sup.22 1.5249                                  2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          121    3-phenoxyacetoxy-5,5-dimethyl-                                                                       n.sub.D.sup.22 1.5369                                  2-cyclohexene-1-one                                                           2-(N-ethoxypropionimidoyl)-                                            122    3-phenylacetoxy-6-isobutyl-                                                                          n.sub.D.sup.24 1.5172                                  2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          123    3-(2,4-dichlorophenoxyacetoxy)-                                                                      n.sub.D.sup.25 1.4082                                  5,5-dimethyl-2-cyclohexene-1-                                                 one                                                                           2-(N-allyloxybutyrimidoyl)-                                            124    3-(2,4-dichlorophenoxyacetoxy)-                                                                      n.sub.D.sup.25 1.5435                                  5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-methylthiomethoxy-                                                125    propionimidoyl)-3-benzoyloxy-                                                                        n.sub.D.sup.25 1.5415                                  5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-methoxymethoxypropionimidoyl)-                                    126    3-benzoyloxy-5,5-dimethyl-2-                                                                         m.p. 84-                                               cyclohexene-1-one      86° C                                           2-(N-methylthiomethoxy-                                                127    propionimidoyl)-3-benzoyloxy-                                                                        n.sub.D.sup.23 1.5495                                  5,5-dimethyl-2-cyclohexene-                                                   1-one                                                                         2-(N-methoxymethoxypropion-                                            128    imidoyl)-3-methylsulfonyloxy-                                                                        n.sub.D.sup.27 1.4886                                  5,5-dimethyl-2-cyclohexene-1-                                                 one                                                                           2-(N-butoxymethoxypropion-                                             129    imidoyl)-3-benzoyloxy-5,5-                                                                            n.sub.D.sup.23 1.5138                                 dimethyl-2-cyclohexene-1-one                                                  2-(N-butoxymethoxypropion-                                             130    imidoyl)-3-methylsulfonyloxy-                                                                        n.sub.D.sup.23 1.4885                                  5,5-dimethyl-2-cyclohexene-1-                                                 one                                                                           2-(N-allyloxypropionimidoyl)-                                          131    3-benzoyloxy-5,5-dimethyl-                                                                           m.p. 60.5-                                             2-cyclohexene-1-one    61.5° C                                         2-(N-allyloxybutyrimidoyl)-                                            132    3-methoxy-5,5-dimethyl-2-                                                                            n.sub.D.sup.26 1.3532                                  cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          133    3-benzoyloxy-5,6-tetramethylene-                                                                     n.sub.D.sup.20.5 1.5499                                2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          134    3-benzoyloxy-5,5-pentamethylene-                                                                     n.sub.D.sup.23 1.5475                                  2-cyclohexene-1-one                                                           2-(N-allyloxypropionimidoyl)-                                          135    3-(2,4-dichlorobenzoyloxy)-5,5-                                                                      m.p. 74-                                               dimethyl-2-cyclohexene-1-one                                                                         75° C                                           2-(N-propargyloxybutyrimidoyl)-                                        136    3-(3,6-dichloro-2-methoxy-                                                                           m.p. 87-                                               benzoyloxy)-5,5-dimethyl-2-                                                                          88° C                                           cyclohexene-1-one                                                             2-(N-allyloxypropionimidoyl)-                                          137    3-(2,4-dichlorobenzoyloxy)-6,6-                                                                      n.sub.D.sup.19 1.5490                                  dimethyl-2-cyclohexene-1-one                                           ______________________________________                                         * m.p.: melting point (° C)                                            d.p.: decomposition point (° C)                                        n.sub.D : refractive index                                               

Hereinafter, the compounds of this invention are represented by CompoundNo. in Table 1.

As mentioned previously, it has been found that the compounds of theinvention possess superior herbicidal activity. The paragraphs whichfollow described in more detail the utility of this invention.

The compounds of the invention are particularly effective in the controlof grass weeds such as annual bluegrass (Poa annua L.), water foxtail(Alopecurus aequalis Sobol), large crabgrass (Digitaria adscendensHenr.), green foxtail (Seturia viridis Beauv), wild oat (Avena fatua L)etc. and they hardly injure broad leaf crops such as adzuki beam(Phaseolus angularis W. F. Wright) and soy bean (Glycine max Merrill)and sugar beets (Beta vulgaris L.) which easily suffer phyto-toxicity.Namely, the compound of the invention are the selective herbicide.

It is already known that 4-hydroxy-6-methyl-α-pyrone derivatives hasherbicidal properties as shown in Japanese Pat. Publication No.16916/1971.

But in order to destroy completely the said grass weeds, a large amountof the above herbicidal chemical is required and this is one drawbackfor above mentioned herbicidal compound.

In the other words, according to the descriptions of above mentionedprior art and the results of the later additional experiments by theinventors, a chemical amount containing 500 g of effective ingredient,in proportion to 10 are ("are" is 100 square meters) of area is able togive an expected effect in the case of employing it practically, butanother chemical amount containing 250 g of effective ingredient, inproportion to 10 are of area is not able to wither grass weeds to death,in the other weeds, it cannot give a perfect herbicidal effect.

But, in the event of employing the compound of the present invention asa herbicide, a chemical amount containing 250 g of effective component,as a matter of course, further a chemical amount containing 125 g orless of effective ingredient, in proportion to 10 are of area, incompliance with the same treating method of conventional herbicideexhibits a strong herbicidal effect and thereby a perfect prevention andextermination of weeds can be expected.

In case of foliar treatment using the compounds of the presentinvention, even the same amount of chemical which kills completelybarnyard grass of grass weeds gives no damages to broadleaf plants suchas radish (Raphanus sativus L.), soy bean, garden pea (Pisum sativumL.), spinach (Spinacia oleracea L.) sugar beets and carrot (Daucuscarota L.) at all, and in case of soil treatment before germination,even the same amount of chemicals which prevents large crab-grassgerminating gives no damages to seeds of broad leaf plants at all.

As mentioned above, a security to the broadleaf crop againstphytotoxicity of the herbicide is extremely high and as to itsapplication, in the other words, its applicable time, its applyinglocation and its applying concentration, it has a very broad extent andit can be used in the wider extent.

It is another advantage of the present invention that a residualtoxicity in the soil or the plant and an acute toxicity for worm bloodedanimals and fish are not feared because the said compounds can be usedwith a low chemical concentration.

The compounds of this invention can be applied directly to the soil aspre-emergence treatment or to plant foliage, as post-emergencetreatment, or they can be mixed intimately with the soil, preferablypost-emergence treatment to plant foliage, and may be applied to soil orplant foliar at rates of 50-1000 g per 10 are, preferably 50-200 g per10 are, more preferably about 100 g per 10 are.

The method of the present invention comprehends the employment of aliquid or solid composition containing one or more of the presentcompounds as an active ingredient.

The active ingredient of this invention may be formulated by mixing withsuitable carriers in a form generally used in agricultural chemicalssuch as wettable powder, emulsifiable concentrate, dust formulation,granular formulation, water soluble powder and aerosol. As solidcarriers, bentonite, diatomaceous earth, apatite, gypsum, talc,pyrophyllite, vermiculite, clay and others are used. As liquid carriers,kerosene, mineral oil, petroleum, solvent naphtha, benzene, xylene,cyclohexane, cyclohexanone, dimethylformamide, alcohol, acetone, andothers are used. Sometimes surface active agent is added in order togive a homogeneous and stable formulation.

The compounds of this invention also can be applied admixed with otherchemicals which are used in agronomic and horticultural management andare compatible with the compounds of this invention. Such chemicals canbe, but are not restricted to, the classes of chemicals commonly knownas plant nutrients, fertilizers, insecticides, acaricides, fungicides,herbicides and nematocides.

As for known herbicides it is recommended that the compound of thepresent invention is applied admixed with urea derivatives such as3-(3,4-dichlorophenyl)-1-methoxy-1-nmethylurea, orN-(3,4-dichlorophenyl)N', N'-dimethylurea, triazine derivatives such as2-chloro-4-ethylamino-6-isopropylamino-s-triazine, or2-chloro-4,6-bis(ethylamino)-s-triazine and amide derivatives such asN-1-naphthyl-phthalamic acid.

The concentrations of the active ingredients in the herbicidalcomposition of this invention vary according to type of formulation, andthey are, for example, used in a range of 5 - 80 weight percent,preferably 10 - 60 weight percent, in wettable powder, 5 - 70 weightpercent, preferably 20 - 60 weight percent, in emulsifiableconcentrates, and 0.5 - 30 weight percent, preferably 1 - 10 weightpercent in dust formulation.

Thus, a wettable powder or an emulsifiable concentrate produced theretois diluted with water to a specified concentration and thereby, it isused as a liquid suspension or a liquid emulsion for treating soils orplant foliars. Further, a dust formulation is directly used for the soiltreatment or the foliar treatment.

The non-limiting examples for the herbicidal composition are illustratedas follows:

EXAMPLE 15 Wettable Powder

    ______________________________________                                                      Parts by weight                                                 ______________________________________                                        Compound 8      20                                                            Diatomaceous earth                                                                            35                                                            Sodium alkylsulfate                                                                            6                                                            Talc            35                                                            White carbon     4                                                            ______________________________________                                    

These are mixed homogeneously and reduced to fine particles.Consequently, wettable powder containing 20% of active ingredient isobtained. In practical use, it is diluted to a certain concentrationwith water and is sprayed as a suspension.

EXAMPLE 16 Emulsifiable Concentrate

    ______________________________________                                                        Parts by weight                                               ______________________________________                                        Compound 1        40                                                          Xylene            33                                                          Dimethylformamide 15                                                          Polyoxyethylene phenylether                                                                     12                                                          ______________________________________                                    

These are mixed and dissolved.

Consequently, emulsifiable concentrate containing 40% of the activeingredient is obtained. In practical use, it is diluted to certainconcentration with water and then is sprayed an emulsion.

EXAMPLE 17 Dust Formulation

    ______________________________________                                                      Parts by weight                                                 ______________________________________                                        Compound 14     5                                                             Talc            38.5                                                          Bentonite       10                                                            Clay            38.5                                                          Sodium alkylsulfate                                                                           8                                                             ______________________________________                                    

These are mixed homogeneously and reduced to fine particles. Fineparticles are made into granules having the diameter in the range of0.5 - 1.0 mm by granulator.

Consequently, dust formulation containing 50% of the active ingredientis obtained. In practical use it is directly applied.

The superior herbicidal effect of the novel compounds of this inventionis clearly illustrated by the following test.

Test 1. Pre-emergence treatment (soil treatment in paddy condition)

About 60 seeds of barnyard grass were planted in a pot having 60 squarecentimeters and covered slightly with soil. Water was poured into thepot until the surface of soil became wet.

10 ml of an aqueous emulsion prepared by diluting an emulsifiableconcentrate with water to a specified concentration was sprayed on thepot. The pots were kept in a green house and water was added to the potsdaily in order to keep the water level. Two weeks after spraying, thedegrees of damage to the plant were observed and estimated by the valuesof 0 - 5 which have the following meanings:

0: no effect

1: partial plant slightly injured

2: plant slightly injured

3: plant moderately injured.

4: plant severely injured

5: plant completely killed or no germination

The results were shown in Table 2.

                                      Table 2                                     __________________________________________________________________________                      Application rate (g/10 ares)                                __________________________________________________________________________    Test Compound No. 30    15    7.5                                             __________________________________________________________________________    1                 5     3     1                                               2                 5     4     3                                               3                 5     4     3                                               4                 4     3     1                                               5                 5     4     3                                               6                 5     3     2                                               7                 4     4     3                                               8                 5     4     3                                               11                5     4     3                                               12                4     3     1                                               13                5     4     3                                               14                5     4     3                                               15                5     5     4                                               16                5     4     4                                               18                4     3     1                                               19                5     4     2                                               20                5     4     3                                               21                4     3     2                                               22                4     3     2                                               23                5     4     3                                               24                4     4     3                                               25                4     3     1                                               26                5     4     3                                               27                5     4     2                                               28                4     3     1                                               29                4     3     2                                               30                5     4     3                                               31                4     4     3                                               32                5     4     3                                               33                5     4     3                                               34                4     2     1                                               35                5     4     3                                               36                5     4     3                                               37                4     3     1                                               39                4     3     2                                               44                5     4     3                                               Comparative                                                                   compound                                                                       ##STR1##         1     0     0                                               Untreated               0                                                     __________________________________________________________________________

Test 2. Post-emergence treatment (foliar treatment in paddy condition)

About 50 seeds of barnyard grass were planted in a pot having 60 squarecentimeters and covered slightly with soil. Said pot was filled withwater to about 3 cm above the surface of the soil when the plant wasgrown to first leaf-stage.

An aqueous emulsion prepared by diluting an emulsifiable concentratewith water to a specified concentration was sprayed on the pot. The potswere kept in a green house and water was added to the pot daily in orderto keep the water level. Two weeks after spraying, the degrees of damageto the test plant was observed and estimted by the values of 0 - 5 whichhave the same meanings as those of Test 1.

The results were shown in Table 3.

                                      Table 3                                     __________________________________________________________________________                        Application rate (g/10 ares)                              __________________________________________________________________________    Test Compound No.   125   62.5  31.5                                          __________________________________________________________________________    1                   5     4     3                                             2                   5     4     2                                             3                   5     5     3                                             4                   5     4     3                                             5                   5     5     3                                             6                   5     5     2                                             7                   5     5     4                                             8                   5     5     5                                             11                  5     4     3                                             12                  5     4     2                                             13                  5     5     2                                             14                  5     5     4                                             15                  5     5     5                                             16                  5     5     5                                             18                  5     4     2                                             19                  5     5     3                                             20                  5     5     4                                             21                  5     5     2                                             22                  5     5     3                                             23                  5     5     5                                             24                  5     4     2                                             25                  5     4     2                                             26                  5     5     3                                             27                  5     4     3                                             28                  5     4     2                                             29                  5     5     4                                             30                  5     5     4                                             31                  5     4     2                                             32                  5     4     3                                             33                  5     5     3                                             34                  5     4     4                                             35                  5     4     2                                             36                  5     5     2                                             37                  5     4     2                                             38                  5                                                         39                  5     4     2                                             40                  5                                                         41                  5                                                         42                  5                                                         43                  5                                                         44                  5     5     2                                             Comparative                                                                   compound                                                                       ##STR2##           3     1     0                                              ##STR3##           3     1     0                                             Untreated                 0                                                   __________________________________________________________________________

Test 3. Pre-emergence treatment

Seeds of large crab-grass were planted in a pot having 100 squarecentimeters. An aqueous emulsion prepared by diluting an emulsifiableconcentrate with water to a specified concentration was sprayed on thesurface of the soil before emergence. The pots were kept in a greenhouse. 21 days after spraying, the degrees of damage to the test plantswere observed and estimated by the value of 0 - 5 which have the samemeanings as those of Test 1.

The results were shown in Table 4.

                                      Table 4                                     __________________________________________________________________________                        Application rate (g/10 ares)                              __________________________________________________________________________    Test Compound No.   250   125   60    30                                      __________________________________________________________________________    1                         5     4     3                                       2                         5     4     2                                       3                         5     5     3                                       4                         5     4     3                                       5                         5     5     3                                       6                         5     5     3                                       7                         5     4     3                                       8                         5     5     3                                       11                        5     4     3                                       12                        4     3     2                                       13                        5     5     3                                       14                        5     4     3                                       15                        5     5     3                                       16                        5     5     3                                       18                        4     4     2                                       19                        5     4     3                                       20                        5     4     3                                       21                        5     4     2                                       22                        5     5     3                                       23                        5     4     3                                       24                        5     4     2                                       25                        5     4     2                                       26                        5     5     3                                       27                        5     4     3                                       28                        4     4     2                                       29                        5     4     2                                       30                        5     5     3                                       31                        4     4     2                                       32                        5     4     2                                       33                        5     4     3                                       34                        5     4     2                                       35                        5     4     3                                       36                        5     4     3                                       37                        5     4     3                                       39                        5     4     2                                       44                        5     4     3                                       Comparative                                                                   compound                                                                       ##STR4##           4     2     0     0                                       Untreated                 0                                                   __________________________________________________________________________

Test 4. Post-emergence treatment (foliar treatment)

Seeds of large crab-grass was planted in a pot having 100 squarecentimeters. When plants became 2 - 4 leaves stage, an aqueous emulsionprepared by diluting an emulsifiable concentrate with water to aspecified concentration was sprayed on the foliar of the test plant at arate of 100 liters per 10 are. The plants were kept in a green house.

21 days after spraying, the degrees of damage to the test plant wereobserved and estimated by the value of 0 - 5 which have the samemeanings as those of Test 1. The results were shown in Table 4.

                                      Table 5                                     __________________________________________________________________________                        Application rate (g/10 ares)                              __________________________________________________________________________    Test Compound No.   100   50    25                                            __________________________________________________________________________    1                   5     5     4                                             2                   5     4     3                                             3                   5     5     5                                             4                   5     3     3                                             5                   5     5     5                                             6                   5     5     4                                             7                   5     5     4                                             8                   5     5     5                                             11                  5     5     4                                             12                  5     5     3                                             13                  5     5     5                                             14                  5     5     4                                             15                  5     5     5                                             16                  5     5     5                                             18                  5     4     3                                             19                  5     5     4                                             20                  5     5     4                                             21                  5     5     4                                             22                  5     5     5                                             23                  5     5     5                                             24                  5     4     4                                             25                  5     3     3                                             26                  5     5     5                                             27                  5     5     4                                             28                  5     3     3                                             29                  5     5     5                                             30                  5     5     4                                             31                  5     3     3                                             32                  5     4     3                                             33                  5     5     5                                             34                  5     3     3                                             35                  5     5     4                                             36                  5     5     5                                             37                  5     4     4                                             39                  5     5     4                                             44                  5     5     4                                             Comparative                                                                   compound                                                                       ##STR5##           3     2     0                                              ##STR6##           3     1     0                                             Untreated                 0                                                   __________________________________________________________________________

What is claimed is:
 1. A compound of the formula ##SPC8##wherein R₁ isselected from the group consisting of phenyl and straight or branchedchain alkyl; R₂ is selected from the group consisting of straight orbranched chain lower alkyl, straight or branched chain lower alkenyl,lower alkynyl, lower alkoxymethyl, lower alkylthiomethyl and benzyl; Ris selected from the group consisting of phenyl and phenyl substitutedwith halogen, nitro, methyl or methoxy.
 2. A compound of the formula##SPC9##wherein R₁ is selected from the group consisting of ethyl andpropyl; R₂ is selected from the group consisting of ethyl, propyl, allyland propargyl; R is selected from the group consisting of phenyl andsubstituted phenyl having at least one substituent selected the groupconsisting of chlorine, methyl, methoxy and nitro. 3.2-(N-allyloxypropionimidoyl)-3-(4-chlorobenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one.4.2-(N-allyloxybutyrimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclohexene-1-one.5.2-(N-allyloxypropionimidoyl)-3-(4-nitrobenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one.6.2-(N-allyloxypropionimidoyl)-3-benzoyloxy-5,5-dimethyl-2-cyclohexene-1-one.7.3-benzoyloxy-5,5-dimethyl-2-N-propargyloxybutyrimidoyl-2-cyclohexene-1-one.8.2-(N-allyloxypropionimidoyl)-3-(3-methoxybenzoyloxy)-5,5-dimethyl-2-cyclohexene-1-one.9.2-(N-allyloxypropionimidoyl)-3-(3-chlorobenzyloxy)-5,5-dimethyl-2-cyclohexene-1-one.10.3-(4-methylbenzoyloxy)-5,5-dimethyl-2-(N-propargyloxybutyrimidoyl)-2-cyclohexene-1-one.11. A method for the control of weeds comprising applying a compositioncontaining a compound of claim 1 in an amount sufficient to exertherbicidal action to a locus to be protected.
 12. A method for thecontrol of weeds comprising applying a composition containing a compoundof claim 2 in an amount sufficient to exert herbicidal action to a locusto be protected.
 13. A method for the control of weeds comprisingapplying a composition containing a compound of claim 3 in an amountsufficient to exert herbicidal action to a locus to be protected.
 14. Amethod for the control of weeds comprising applying a compositioncontaining a compound of claim 4 in an amount sufficient to exertherbicidal action to a locus to be protected.
 15. A method for thecontrol of weeds comprising applying a composition containing a compoundof claim 5 in an amount sufficient to exert herbicidal action to a locusto be protected.
 16. A method for the control of weeds comprisingapplying a composition containing a compound of claim 6 in an amountsufficient to exert herbicidal action to a locus to be protected.
 17. Amethod for the control of weeds comprising applying a compositioncontaining a compound of claim 7 in an amount sufficient to exertherbicidal action to a locus to be protected.
 18. A method for thecontrol of weeds comprising applying a composition containing a compoundof claim 8 in an amount sufficient to exert herbicidal action to a locusto be protected.
 19. A method for the control of weeds comprisingapplying a composition containing a compound of claim 9 in an amountsufficient to exert herbicidal action to a locus to be protected.
 20. Amethod for the control of weeds comprising applying a compositioncontaining a compound of claim 10 in an amount sufficient to exertherbicidal action to a locus to be protected.